Brattleboro, VT Homes

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  /59

  $543,000 Sold Aug 07, 2025

  628 S Main St, Brattleboro, VT 05301

  • 5 Beds
  • 4.5 Baths
  • 5,850 Sq Ft
  • Built 2000

  Last Sold Summary

  • 1% Below List Price
  • $93/SF
  • 20 Days On Market

  Last Listing Agent Kerry Mulverhill

  628 S Main St, Brattleboro, VT 05301
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  /32

  Est $197,770 Not Listed For Sale

  36 Augur Hole Rd, Brattleboro, VT 05301

  • 2 Beds
  • 1 Bath
  • 920 Sq Ft
  • Built 1948

  36 Augur Hole Rd, Brattleboro, VT 05301

  Last Sold Summary

  • 16% Above List Price
  • $185/SF
  • 8 Days On Market

  Last Sold Price $170,000

  Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty
• 

  

  

  /23

  $159,000 Coming Soon

  • 1 Bed
  • 1 Bath
  • 592 Sq Ft

  219 High St Unit 3, Brattleboro, VT 05301

  Welcome to the effortless existence of condominium life with the rare addition of uniqueness. How nice to own a home while splitting the expenses with two other condo owners. Park in your driveway and follow a pretty stone path to your first-floor sanctuary. This efficient 592 sq ft space offers an open kitchen, dining area with a washer and dryer, living room, one bedroom, and a full bath. Share

  Kristen Ziter Taylor Brattleboro Area Realty

  219 High St Unit 3, Brattleboro, VT 05301
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  /23

  $180,000 Sold May 23, 2025

  39 Brookside Dr Unit 5, Brattleboro, VT 05301

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft
  • Built 1966

  Last Sold Summary

  • $194/SF
  • 49 Days On Market

  Current Estimated Value $191,093

  Last Listing Agent Angela Sherman Brattleboro Area Realty

  39 Brookside Dr Unit 5, Brattleboro, VT 05301
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  /31

  Est $264,661 Not Listed For Sale

  196 Randall Dr, Brattleboro, VT 05301

  • 3 Beds
  • 1 Bath
  • 1,335 Sq Ft
  • Built 1973

  196 Randall Dr, Brattleboro, VT 05301

  Last Sold Summary

  • 2% Above List Price
  • $195/SF
  • 87 Days On Market

  Last Sold Price $260,000

  Last Listing Agent Christine Lewis Brattleboro Area Realty
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  /14

  $120,000 Under Contract

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  60 Brookside Dr Unit 1, Brattleboro, VT 05301

  Rare opportunity to own a desirable end-unit condo in a prime Brattleboro location, priced to sell. This well-maintained unit offers added privacy and natural light, along with a private deck overlooking the river, creating a peaceful setting to relax and enjoy the surrounding landscape. Ideally situated within walking distance to the Brattleboro Farmers Market, Memorial Park, and the Vermont

  Morriah Adams BHG Masiello Brattleboro

  60 Brookside Dr Unit 1, Brattleboro, VT 05301
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  /20

  $79,000 Sold May 05, 2025

  6 Thistle Hill Rd, Brattleboro, VT 05301

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft
  • Built 1986

  Last Sold Summary

  • $101/SF
  • 8 Days On Market

  Last Listing Agent Victoria Woods Brattleboro Area Realty

  6 Thistle Hill Rd, Brattleboro, VT 05301
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  /22

  Est $285,497 Not Listed For Sale

  1075 Middle Rd, Brattleboro, VT 05301

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 1968

  1075 Middle Rd, Brattleboro, VT 05301

  Last Sold Summary

  • 2% Below List Price
  • $336/SF
  • 7 Days On Market

  Last Sold Price $290,000

  Last Listing Agent Julie Lowe Lowe's Real Estate, LLC
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  /2

  $350,000

  • 2 Beds
  • 1 Bath
  • 3,312 Sq Ft

  573 S Main St, Brattleboro, VT 05301

  Just around the corner! From the middle and high school, Oak groveelementary! Pop around the corner for all the high school games,exercise at the track. Interstate is minutes away for easy access towork or play! One apartment is over 1,000 square feet so tons of roomfor owner occupancy! 2 nice front porches. Worth looking at for eitheryour own home or as an investment. Masks

  Christine Lewis Brattleboro Area Realty

  573 S Main St, Brattleboro, VT 05301
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  /43

  $229,300 Sold May 02, 2025

  129 Morningside Commons, Brattleboro, VT 05301

  • 2 Beds
  • 2 Baths
  • 1,139 Sq Ft
  • Built 1998

  Last Sold Summary

  • $201/SF
  • 28 Days On Market

  Current Estimated Value $246,149

  Last Listing Agent Zachary Zupan EXP Realty

  129 Morningside Commons, Brattleboro, VT 05301
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  /12

  Est $235,494 Not Listed For Sale

  129 West St, Brattleboro, VT 05301

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft
  • Built 1891

  129 West St, Brattleboro, VT 05301

  Last Sold Summary

  • 12% Above List Price
  • $227/SF
  • 18 Days On Market

  Last Sold Price $210,000

  Last Listing Agent John Hatton Berkley & Veller Greenwood Country
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  /28

  $269,000 Under Contract

  • 4 Beds
  • 1 Bath
  • 1,374 Sq Ft

  15 West St, Brattleboro, VT 05301

  Enjoy a spacious kitchen that flows seamlessly into a large living area with open views of Mount Wantastiquet. This single-level ranch offers four generously sized bedrooms and a full bath, making it ideal for those seeking one-floor living and efficient heating. A cozy woodstove in the living area helps offset heating costs while adding warmth and charm. Hardwood flooring, a beautifully tiled

  Liz LaVorgna Brattleboro Area Realty

  15 West St, Brattleboro, VT 05301
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  /28

  $460,000 Sold May 01, 2025

  70 Tyler St, Brattleboro, VT 05301

  • 4 Beds
  • 1.5 Baths
  • 2,051 Sq Ft
  • Built 1920

  Last Sold Summary

  • $224/SF
  • 0 Days On Market

  Current Estimated Value $471,510

  Last Listing Agent Karen Hoppe Berkley & Veller Greenwood Country

  70 Tyler St, Brattleboro, VT 05301
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  /40

  Est $343,911 Not Listed For Sale

  36 Goldfinch Ln, Brattleboro, VT 05301

  • 4 Beds
  • 1.5 Baths
  • 1,716 Sq Ft
  • Built 1935

  36 Goldfinch Ln, Brattleboro, VT 05301

  Last Sold Summary

  • 17% Above List Price
  • $172/SF
  • 17 Days On Market

  Last Sold Price $295,000

  Last Listing Agent Meg Streeter Meg Streeter Real Estate
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  /8

  $48,000

  • Land
  • 6.1 Acres
  • $7,869 per Acre

  0 Cooke Rd, Brattleboro, VT 05301

  Amidst rolling VT farmland, sits these 6 acres in West Brattleboro. While there is road frontage on Rte 9, the driveway is off the class 4 section of Cooke Rd. There's about 250 feet of Cooke Rd that you would need to maintain before the town road. The ROW into the land parallels the power lines, which you cannot see when you're on the land. There a nice cleared shelf when you walk in and then

  Victoria Woods Brattleboro Area Realty

  0 Cooke Rd, Brattleboro, VT 05301
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  /39

  $475,000 Sold Apr 23, 2025

  101 Washington St, Brattleboro, VT 05301

  • 5 Beds
  • 2.5 Baths
  • 2,823 Sq Ft
  • Built 1905

  Last Sold Summary

  • $168/SF
  • 121 Days On Market

  Current Estimated Value $490,807

  Last Listing Agent Thomas Dahlin Berkley & Veller Greenwood Country

  101 Washington St, Brattleboro, VT 05301
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  /32

  Est $319,646 Not Listed For Sale

  499 S Main St, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1980

  499 S Main St, Brattleboro, VT 05301

  Last Sold Summary

  • $317/SF
  • 9 Days On Market

  Last Sold Price $320,000

  Last Listing Agent Kerry Mulverhill
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  /2

  $370,000

  • 5 Beds
  • 4 Baths
  • 3,002 Sq Ft

  10 Birge St, Brattleboro, VT 05301

  Invest in your own home town! Full tenant roster with the easy access to laundry across the street, grocery stores, train and The Moover. Right in the heart of things with little yard to maintain! Consider as an investment in your portfolio or decide to live in one unit and have the others pay your mortgage! Good way to start, retire or increase your portfolio! Owner is a licensed appraiser.

  Christine Lewis Brattleboro Area Realty

  10 Birge St, Brattleboro, VT 05301
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  /22

  $89,900 Sold Jan 23, 2026

  2 Wagon Dr, Brattleboro, VT 05301

  • 2 Beds
  • 2 Baths
  • 910 Sq Ft
  • Built 1977

  Last Sold Summary

  • $99/SF
  • 6 Days On Market

  Last Listing Agent Christine Lewis Brattleboro Area Realty

  2 Wagon Dr, Brattleboro, VT 05301
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  /27

  Est $236,701 Not Listed For Sale

  379 S Main St, Brattleboro, VT 05301

  • 3 Beds
  • 1 Bath
  • 1,665 Sq Ft
  • Built 1850

  379 S Main St, Brattleboro, VT 05301

  Last Sold Summary

  • 58% Above List Price
  • $90/SF
  • 137 Days On Market

  Last Sold Price $150,000

  Last Listing Agent Christine Lewis Brattleboro Area Realty
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  /48

  $415,000 Under Contract

  • 6 Beds
  • 2 Baths
  • 2,048 Sq Ft

  58-60 Frost Place, Brattleboro, VT 05301

  This turnkey income generator is now move in ready! One side is vacant and ready for your plans, the other has a successful Airbnb rental history and was completely renovated in 2018. Brand new hot water heater, dishwasher, garbage disposal, and toilet have just been installed. Both have in-unit washer & dryer. Enter through the thoughtfully crafted mudrooms with generous built-in storage. The

  Lily Gautot Greenwald Realty Group

  58-60 Frost Place, Brattleboro, VT 05301
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  /12

  $325,000 Sold Feb 20, 2026

  16 Sycamore St, Brattleboro, VT 05301

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1992

  Last Sold Summary

  • 1% Below List Price
  • $339/SF
  • 10 Days On Market

  Current Estimated Value $317,750

  Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

  16 Sycamore St, Brattleboro, VT 05301
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  /23

  Est $301,684 Not Listed For Sale

  380 S Main St, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 1,539 Sq Ft
  • Built 1910

  380 S Main St, Brattleboro, VT 05301

  Last Sold Summary

  • 10% Above List Price
  • $179/SF
  • 7 Days On Market

  Last Sold Price $275,000

  Last Listing Agent Stephanie Peduzzi-Baker Brattleboro Area Realty
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  /51

  $899,800

  • 5 Beds
  • 8 Baths
  • 7,430 Sq Ft

  925 Hinesburg Rd, Brattleboro, VT 05301

  Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

  Christine Lewis Brattleboro Area Realty

  925 Hinesburg Rd, Brattleboro, VT 05301
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  /33

  $455,000 Sold Mar 04, 2026

  139 Buttonwood Dr, Brattleboro, VT 05301

  • 2 Beds
  • 2 Baths
  • 1,390 Sq Ft
  • Built 2014

  Last Sold Summary

  • 4% Below List Price
  • $327/SF
  • 6 Days On Market

  Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

  139 Buttonwood Dr, Brattleboro, VT 05301
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  /12

  Est $345,772 Not Listed For Sale

  71 Home St, Brattleboro, VT 05301

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • Built 1993

  71 Home St, Brattleboro, VT 05301

  Last Sold Summary

  • 1% Below List Price
  • $189/SF
  • 47 Days On Market

  Last Sold Price $348,400

  Last Listing Agent John Hatton Berkley & Veller Greenwood Country
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  /3

  $125,000

  • Land
  • 1.75 Acres
  • $71,429 per Acre

  0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301

  Manicured into a beautiful high meadow, in a nice little neighborhood....sunny with views, what morecould you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor

  Christine Lewis Brattleboro Area Realty

  0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301
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  /19

  $305,000 Sold Aug 05, 2025

  85 Crosby St, Brattleboro, VT 05301

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft
  • Built 1950

  Last Sold Summary

  • 2% Above List Price
  • $203/SF
  • 41 Days On Market

  Current Estimated Value $312,543

  Last Listing Agent Karen Hoppe Berkley & Veller Greenwood Country

  85 Crosby St, Brattleboro, VT 05301
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  /24

  Est $242,925 Not Listed For Sale

  46 Moreland Ave, Brattleboro, VT 05301

  • 2 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1956

  46 Moreland Ave, Brattleboro, VT 05301

  Last Sold Summary

  • 4% Below List Price
  • $222/SF
  • 97 Days On Market

  Last Sold Price $254,000

  Last Listing Agent Tim Berg Brattleboro Area Realty
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  /37

  $795,000

  • 4 Beds
  • 4 Baths
  • 3,600 Sq Ft

  5 Hillwinds N, Brattleboro, VT 05301

  Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on 11 acres of landscaped grounds with lawns, stone walls, gardens, and woodland in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered porch that opens into a marble floored foyer

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, Brattleboro, VT 05301
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  /56

  $240,000 Sold Aug 29, 2025

  67 Morningside Commons, Guilford, VT 05301

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft
  • Built 1988

  Last Sold Summary

  • 2% Above List Price
  • $227/SF
  • 19 Days On Market

  Current Estimated Value $238,054

  Last Listing Agent Sally Fegley BHG Masiello Brattleboro

  67 Morningside Commons, Guilford, VT 05301
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  /16

  Est $393,492 Not Listed For Sale

  68 Wilsons Woods Rd, Brattleboro, VT 05301

  • 3 Beds
  • 1 Bath
  • 1,722 Sq Ft
  • Built 1999

  68 Wilsons Woods Rd, Brattleboro, VT 05301

  Last Sold Summary

  • 4% Below List Price
  • $239/SF
  • 7 Days On Market

  Last Sold Price $412,000

  Last Listing Agent A.J. Bellville Bellville Realty
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  /18

  $285,000

  • 1 Bed
  • 1 Bath
  • 1,320 Sq Ft

  116 Birge St Unit 2, Brattleboro, VT 05301

  Simple but elegant! Historic posts and wonderful beams define the magnificent open concept, giving visual shape and creating traditional options or whimsical uses for your new lifestyle. High ceilings and huge windows create a celebration of light, complementing the glowing antique floors—magical in combination and truly beautiful. A home, an artist loft...so many uses, so unique, so

  Christine Lewis Brattleboro Area Realty

  116 Birge St Unit 2, Brattleboro, VT 05301
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  /10

  $145,000 Sold Jan 06, 2026

  680 W River Rd, Brattleboro, VT 05301

  • Land
  • 8 Acres
  • $18,125 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 148 Days On Market

  Last Listing Agent Chris Long BHG Masiello Brattleboro

  680 W River Rd, Brattleboro, VT 05301
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  /40

  Est $450,371 Not Listed For Sale

  67 Wilsons Woods Rd, Brattleboro, VT 05301

  • 5 Beds
  • 3 Baths
  • 1,444 Sq Ft
  • Built 2004

  67 Wilsons Woods Rd, Brattleboro, VT 05301

  Last Sold Summary

  • 3% Below List Price
  • $321/SF
  • 7 Days On Market

  Last Sold Price $464,000

  Last Listing Agent Kathy Dowd Bellville Realty
• 

  

  /19

  $295,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,850 Sq Ft

  70 Arbor Hill Commons Unit 14, Brattleboro, VT 05301

  Welcome to Arbor Hill- a 55 and older community of thoughtfully designed and cared for condominiums. Enter the inviting "Bluebell" building on the ground level and take either the stairs or the elevator to the second/top floor. Down the quiet hall you will find the beautiful unit #14. This delightful unit has seen recent renovations totaling $51K+ since 2023, including new flooring and a

  Stephanie Peduzzi-Baker Brattleboro Area Realty

  70 Arbor Hill Commons Unit 14, Brattleboro, VT 05301
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  /60

  $625,000 Sold Oct 03, 2025

  49 Tyler St, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 2,731 Sq Ft
  • Built 1880

  Last Sold Summary

  • 14% Below List Price
  • $229/SF
  • 65 Days On Market

  Current Estimated Value $599,512

  Last Listing Agent Karen Hoppe Berkley & Veller Greenwood Country

  49 Tyler St, Brattleboro, VT 05301
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  /30

  Est $396,307 Not Listed For Sale

  49 Marlboro Ave, Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 1,719 Sq Ft
  • Built 1948

  49 Marlboro Ave, Brattleboro, VT 05301

  Last Sold Summary

  • 12% Above List Price
  • $205/SF
  • 10 Days On Market

  Last Sold Price $352,500

  Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty
• 

  

  /18

  $285,000

  • 3 Beds
  • 1 Bath
  • 1,323 Sq Ft

  164 Chestnut St, Brattleboro, VT 05301

  Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with sliders

  Christine Lewis Brattleboro Area Realty

  164 Chestnut St, Brattleboro, VT 05301
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  /41

  $545,000 Sold Jul 18, 2025

  441 Guilford St, Brattleboro, VT 05301

  • 4 Beds
  • 2 Baths
  • 2,450 Sq Ft
  • Built 1880

  Last Sold Summary

  • 1% Below List Price
  • $222/SF
  • 48 Days On Market

  Current Estimated Value $549,967

  Last Listing Agent Dan Normandeau Berkley & Veller Greenwood Country

  441 Guilford St, Brattleboro, VT 05301

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